u/Cheap_Comfort_1957

Always. And specifically ask for a contractor inspection not just the general home inspector's opinion.

General home inspectors flag obvious issues but rarely get on the roof and rarely catch flashing problems, failed pipe boots, or early stage decking damage. A roofing contractor who physically walks the roof gives you a completely different level of detail.

In Northwest Indiana where weather is hard on roofs, buying a home with a roof that needs attention in the next two years without knowing it is a $10,000 to $20,000 surprise. A contractor inspection before closing typically costs nothing if the contractor offers free assessments and can save you serious negotiating leverage or protect you from a bad deal entirely.